Diastereomeric 7-ureidoacetyl cephalosporins. I. Superiority of 7.ALPHA.-H-L-isomers over D-isomers.
- 1 January 1978
- journal article
- research article
- Published by Japan Antibiotics Research Association in The Journal of Antibiotics
- Vol. 31 (6) , 546-560
- https://doi.org/10.7164/antibiotics.31.546
Abstract
The synthesis and in vitro structure-activity relationship of 7-ureidoacetyl cephalosporins carrying various substituents in the 3-position, compounds that showed an enhanced broad spectrum of antibacterial activity, was outlined. Contrary to most of the previous observations with diastereomeric isomers of cephalosporins, the L-side chain isomers also are very potent antibiotics and are even more active inhibitors of certain .beta.-lactamase-producing gram-negative bacteria than the corresponding D-side chain isomers. SQ 69,613, 7.beta.-[[L-[(aminocarbonyl)amino]-2-furanylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Na salt, the most active compound tested, except for activity against staphylococci, was as active in vitro as cefamandole.This publication has 4 references indexed in Scilit:
- Analysis of diastereomeric 7-ureidoacetamido cephalosporins by high-performance liquid chromatographyJournal of Chromatography A, 1978
- Diastereomeric 7-ureidoacetyl cephalosporins. III. Contribution of D- and L-isomers to the growth inhibiting activities of 7.ALPHA.-H and 7.ALPHA.-OCH3 derivatives for gram-positive and gram-negative bacteria.The Journal of Antibiotics, 1978
- Diastereomeric 7-ureidoacetyl cephalosporins. II. 7.BETA.[[[(Aminocarbonyl) amino]-2-thienylacetyl] amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl) thio] methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid.The Journal of Antibiotics, 1978
- Chemistry of Cephalosporin Antibiotics. VII. Synthesis of Cephaloglycin1 and Some HomologsJournal of Medicinal Chemistry, 1966